2-amino-9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl}-6,9-dihydro-3H-purin-6-one

• ChemBase编号: 133594
• 分子式: C10H12N5O7P
• 平均质量: 345.205341
• 单一同位素质量: 345.04743438
• SMILES: c1nc2c(n1C1C(C3C(O1)COP(=O)(O3)O)O)[nH]c(nc2=O)N
• Canonical SMILES: OC1C2OP(=O)(O)OCC2OC1n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)
• InChIKey: ZOOGRGPOEVQQDX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-6,9-dihydro-3H-purin-6-one
• IUPAC传统名: cyclic guanosine monophosphate
• 别名: cGMP; cyclic GMP; Guanosine 3′,5′-cyclic monophosphate

登记号

• CAS号: 7665-99-8
• EC号: 231-641-6
• MDL号: MFCD00070129
• PubChem SID: 162227871; 24895309
• PubChem CID: 295

理论计算性质

• Acid pKa: 1.762072
• 质子受体: 9
• 质子供体: 4
• LogD (pH = 5.5): -3.7717755
• LogD (pH = 7.4): -3.887292
• Log P: -2.3542986
• 摩尔折射率: 71.2816 cm^3
• 极化性: 27.9194 Å^3
• 极化表面积: 170.52 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 1% NaHCO3: soluble50 mg/mL
• 外观: white powder

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 22-26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)

详细说明

Sigma Aldrich - G7504

Biochem/physiol Actions
An important second messenger, cGMP is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Cyclic GMP interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases. A primary action of elevated cGMP levels in vivo is the stimulation of cGMP-dependent protein kinase (PKG).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G7504.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.